8-methoxy-2H-benzo[e][1,4]dioxepin-5(3H)-one | 1248498-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 8-methoxy-2H-benzo[e][1,4]dioxepin-5(3H)-one
• 英文别名: 8-Methoxy-2,3-dihydro-1,4-benzodioxepin-5-one；8-methoxy-2,3-dihydro-1,4-benzodioxepin-5-one
• CAS: 1248498-26-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: CPTQKGSSAHISNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-hydroxyethoxy)-4-methoxybenzaldehyde 在 4-methyl-3-(2,4,6-trimethylphenyl)thiazolium perchlorate 、 三乙胺 、 偶氮苯 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以90%的产率得到8-methoxy-2H-benzo[e][1,4]dioxepin-5(3H)-one
  参考文献：
  名称：

  Efficient Catalytic, Oxidative Lactonization for the Synthesis of Benzodioxepinones Using Thiazolium-Derived Carbene Catalysts

  摘要：

  An efficient, oxidative carbene-catalyzed lactonization reaction has been developed. Using thiazolium precatalysts, a variety of benzodioxepinone products are accessible in good to excellent yields under mild and operationally simple conditions The reaction does not require high dilution conditions and proceeds via mild and selective oxidation with azobenzene, which can easily be recovered and reused applying inexpensive FeCl3 as a formal terminal oxidant

  DOI：

  10.1021/ol101854r

文献信息

• From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)–C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air
  作者：Xiaoqiang Huang、Xinyao Li、Miancheng Zou、Song Song、Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1021/ja5073004

  日期：2014.10.22

  The Cu-catalyzed aerobic oxidative esterification of simple ketones via C-C bond cleavage has been developed. Varieties of common ketones, even inactive aryl long-chain alkyl ketones, are selectively converted into esters. The reaction tolerates a wide range of alcohols, including primary and secondary alcohols, chiral alcohols with retention of the configuration, electron-deficient phenols, as well

  已经开发了通过 CC 键裂解的 Cu 催化的简单酮的有氧氧化酯化。各种常见的酮，甚至是惰性的芳基长链烷基酮，都被选择性地转化为酯。该反应耐受多种醇，包括伯醇和仲醇、保留构型的手性醇、缺电子酚以及各种天然醇。使用廉价的铜催化剂、广泛的基材范围以及中性和露天条件使该协议非常实用。(18)O 标记实验表明，在这种转化过程中发生了氧化作用。初步机制研究表明，该过程主要涉及两条新途径。
• Efficient Catalytic, Oxidative Lactonization for the Synthesis of Benzodioxepinones Using Thiazolium-Derived Carbene Catalysts
  作者：Christopher A. Rose、Kirsten Zeitler

  DOI：10.1021/ol101854r

  日期：2010.10.15

  An efficient, oxidative carbene-catalyzed lactonization reaction has been developed. Using thiazolium precatalysts, a variety of benzodioxepinone products are accessible in good to excellent yields under mild and operationally simple conditions The reaction does not require high dilution conditions and proceeds via mild and selective oxidation with azobenzene, which can easily be recovered and reused applying inexpensive FeCl3 as a formal terminal oxidant